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Ticklish Business Top 5: Favorite Jack Lemmon Movies

If you’ve listened to the podcast with any frequency, you’ll know that we love to talk about Jack Lemmon. We love a good adorable Jack Lemmon story. It’s just how we roll. As today would have been his 96th birthday, we wanted to sit down and talk about our favorites in his long and formidable filmography.

With a career lasting more than fifty years and posessing an ability to leap across genres in a single bound, no one’s list of Jack Lemmon classics is going to look exactly the same. So without further ado, let’s get to the picks!

Under the Yum Yum Tree (1963)

This is a movie I’m always surprised doesn’t get talked about more in the Jack Lemmon pantheon of delightfulness. Under the Yum Yum Tree is an early 1960s sex comedy starring Lemmon opposite Carol Lynley, Dean Jones, Edie Adams, Imogene Coca, and Paul Lynde.

The movie follows a young couple (Jones and Lynley) who resolve to play-house. However, their plan is to remove the physical from their relationship as a test of their bond. However, when their lothario landlord (Lemmon) gets wind of the situation, romantic complications ensue.

The cast here is top-notch and is certainly a big factor in my enjoyment of this movie. Lemmon hones in on this character and has a lot of fun in his portrayal. Vintage Disney fans will potentially enjoy this one thanks to the presence of a baby Dean Jones who is pitch-perfect as Lynley’s slightly befuddled fiancee. This is also a must for classic TV fans… you can’t beat Paul Lynde and Imogene Coca sharing the screen.

Mister Roberts (1955)

I’ve written about Mister Roberts before, so regular Ticklish Business readers should know my love for this military dramedy following the crew of a supply ship in the Pacific during World War II.

Jack Lemmon shines in this movie as Ensign Pulver. In fact, he took home his first Oscar for his work in this picture as Best Supporting Actor. The movie features a sterling cast including Henry Fonda, William Powell, James Cagney, Betsy Palmer, Nick Adams, and Martin Milner. Mister Roberts comes from director John Ford.

The movie is a sensitive comedy that easily juggles not only the emotions and tension of a war drama but slapstick comedy as well. I’ve written before how the “dramedy” can certainly be a challenge for me, but Mister Roberts has always been a favorite of mine, thanks to Jack Lemmon’s beautiful performance. Check this one out if you haven’t.

The Great Race (1965)

The Great Race tracks alongside Grumpy Old Men was one of my introductions to Jack Lemmon. I’ve been watching this movie for almost as long as I can remember and I’ve said before, my love for The Great Race knows no bounds. I’m going to say it… Jack Lemmon should have been in Oscar consideration for the dual role he plays in this period comedy.

The Great Race has a simple premise… it follows early 20th century daredevils The Great Leslie (Tony Curtis) and Professor Fate as they engage in an automobile race between New York and Paris. However, when a young suffragette (Natalie Wood) forces her way into the race hoping to make a political point, things grow much more complicated.

This movie is a comedy gem that doesn’t get nearly the love it deserves. It features a stacked cast, including Keenan Wynn, Peter Falk, Ross Martin, Vivan Vance, Dorothy Provine, Larry Storch, and others. And come on… don’t you want to see the greatest pie fight ever captured on celluloid?

Grumpy Old Men (1993)

Grumpy Old Men was my introduction to not only Jack Lemmon, but also Walter Matthau, Burgess Meredith, and very likely Ann-Margret. I would have been seven years old when this movie came out in theaters and I remember going to see it. And I loved it! Yes, readers, I was that kid. They really didn’t understand me in elementary school. As I think back on it, Grumpy Old Men was very likely a gateway film for me. It opened my eyes to a lot of classic films and I’m still here as a result.

Grumpy Old Men follows feuding neighbors John (Lemmon) and Max (Matthau). They’ve known each other for years, but they’re just… Grumpy Old Men. Things get more complicated when a foxy artist (Ann-Margret) moves in next door. Which man will be able to land this sultry retiree?

This was the first in a stretch of these nostalgic, retiree gems in the 90s. I mention another in the next entry. However, there are multiple I wanted to talk about, but kids… there just isn’t space. If this list had an ‘Honorable Mention’ category… Out to Sea would be the first mentioned.

My Fellow Americans (1996)

If you follow me on Twitter, you will know my love of My Fellow Americans. I make sure to drop references from this little gem whenever I can. It’s a timeless treasure… yes I mean that. I could quote from it all day.

Don’t say ‘freaking’ Russ, if you have to use the F-word, go for the gold!

Margaret Kramer (Lauren Bacall)

My Fellow Americans follows ex-presidents Douglas (James Garner) and Kramer (Lemmon). They’ve been feuding political rivals for a number of years. However, they’re forced to form a united front when they find themselves involved in a political scandal surrounding the sitting president (Dan Aykroyd). Will this Democrat and Republican be able to put their differences aside in order to survive?

With a cast including luminaries like Lauren Bacall, Wilford Brimley, John Heard, and Sela Ward, this is one fans of all things nostalgic should check out. It’s a delightful little movie… and to be perfectly frank, its handling of partisan politics is something we need in the 2020s.


Well, that brings us to a close. Jack Lemmon, it really doesn’t need to be said again (but here it goes!) was a Hollywood treasure we didn’t deserve. His name toplines some real classics and he brought a charisma and likability which will never be forgotten. This list is a top 5, but it remains to be said that there are lots we didn’t cover here and plenty to talk about in his lengthy career.

Happy birthday, Jack.

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2 thoughts on “Ticklish Business Top 5: Favorite Jack Lemmon Movies Leave a comment

  1. I’m a big fan of Grumpy Old Men, but also Jack’s early work especially, It Should Happen To You, Operation Madball and It Happened to Jane. Have you seen his turn in the western Cowboy? There was nothing Jack couldn’t do.

    • I need to rewatch Cowboy! I have watched it, but it has been years. It Should Happen to You is also one I need to revisit. Thank you for planting those seeds! Those are going on the rewatch list.

      It Happened to Jane is delightful. I’m a sucker for all the classic tv references and I just first time watched Operation Madball not to long ago. He was truly so so so versatile.

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